Substituent effects on the stabilities of phenoxyl radicals and the acidities of phenoxyl radical cations

Autor:	Frederick G. Bordwell, J.-P. Cheng
Rok vydání:	1991
Předmět:	Stereochemistry Radical Substituent General Chemistry Phenoxyl radical Biochemistry Medicinal chemistry Bond-dissociation energy Catalysis Homolysis Ion chemistry.chemical_compound Colloid and Surface Chemistry chemistry Phenols
Zdroj:	Journal of the American Chemical Society. 113:1736-1743
ISSN:	1520-5126 0002-7863
Popis:	Oxidation potentials for 35 phenoxide ions and 3 naphthoxide ions have been combined with their pK HA values to estimated homolytic bond dissociation energies (BDEs) for the O-H bonds in phenols. Comparison with literature values shows that there is remarkably good agreement ΔBDE values determined by different methods. A good correlation of E ox (A − ) values for p-GC 6 H 4 O − phenoxide ions with σ + constants was observed over a range of greater than 40 kcal/mol. The acidities of 35 phenoxyl radical cations have been estimated from pK HA , E ox (A − ), and E ox (HA) values. A good correlation of E ox (HA) vs pK HA •+ was observed from m-GC 6 H 4 OH •+ radical cations, but the points for para donors were found to deviate from the line
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::4f1f4c2f4e63dd10580f6fe3bc2d230f https://doi.org/10.1021/ja00005a042 Zobrazit plný text záznamu